Twice Lucky - Cover

Twice Lucky

Copyright© 2003 by Joe J

Chapter 11

Time Travel Sex Story: Chapter 11 - If you knew then what you know now, how would you act?

Caution: This Time Travel Sex Story contains strong sexual content, including mt/ft   Ma/ft   mt/Fa   ft/ft   Fa/ft   Consensual   Romantic   BiSexual   Time Travel   DoOver   Incest   Brother   Sister   Safe Sex   Oral Sex   Anal Sex   Pregnancy  

Saturday dawned sunny and surprisingly cool. Angie rousted Jake out of bed at 6:45 and by 7:15 they were pounding the pavement on a six-mile run. Angie kept upping the speed and Jake happily let her set the pace. They sprinted the last quarter mile and walked around the block to cool down. Angie told Jake that running helped her cramps and she appreciated his company. She coyly told him she might have a way to make it up to him in about a week. The sweaty duo walked to the back of the house to check on the progress of the pool. According to the contractor, they should be swimming in it next week. He said the propane heater Charles had insisted on would allow them to swim most of the year if they used the pool cover to keep in the heat. It would have felt good that morning to the siblings.

After breakfast the women scattered, Helen and Angie were going shopping and Debbie had some mumbled thing to do. Charles and Jake were shooting the shit about the game last night when Sara called for Jake. She asked him if he could get a ride over to her house that morning because she had a present for him. Jake covered the mouthpiece and asked his dad. Charles said that he had a quarter to ten tee time and could drop him off. Jake relayed the time to Sara and she said the door would be open and his present in her bedroom. Jake had a feeling that he knew what he was getting and hurried upstairs to shower and dress.

Charles dropped Jake off forty-five minutes later with a ‘good luck, sport’, and headed for the country club. Jake glanced at Sara’s black Chevelle with envy and went through the door towards the bedroom shedding clothes as he went. He bounded through the door naked as a jaybird.

“Hi, honey, I’m home,” he said lamely.

“Surprise!” said Debbie.

Jake stopped grinning and stood there goggle-eyed. This definitely was not the present he expected. Debbie was lying in the center of the bed wearing a white nightie with a big bow stuck to the lacy bodice. On the nightstand were a fresh towel and the biggest bottle of baby oil he had ever seen.

Debbie held out her arms, “Come here, baby brother, we have some unfinished business.”

He was there in a flash. Debbie opened her arms to him and they kissed. Jake started to lick and suck his way to her breasts. He untied the sash at the top of the nightgown with his teeth and pulled it open the same way. With the top of the gown pulled open Jake attacked her breasts with his lips and teeth. He gave her little sucks then nipped at her firm orbs. Jake slid his hand to the hem of her gown then under it to her pussy. She was hot, wet, and bald as a baby.

“Sara shaved me this morning for you,” Debbie said.

Jake started to move his face between her legs but Debbie grabbed his head and pulled his lips back to hers.

“We can do that later, Jake. Right now I want you in me. Now make love to me.”

She sat up, Jake helped her pull the gown over her head, and Debbie lay back on the bed. Jake drank in her beauty. Her long thick auburn hair fanned out on the pillow and her slightly tanned skin was smooth and unblemished. Her breasts were firm and barely drooped to the sides, her stomach was smooth and taunt, and her newly-shaved pussy was plump and pink. She held up her arms and he moved over her. She looked at him with lust and a little apprehension.

“Put it in,” he said, “I’ll go slow and won’t hurt you.”

She nodded and reached down and gently took his stalk. She put the head of his shaft against her pussy lips and moved it up and down until it slipped inside her slightly. Jake flexed his hip and the flared crown pushed into her. Despite her wetness, she was virgin-tight. Her eyes widened as he pushed again and an inch of his cock spread her open. She sighed, moaned, and pushed up to him as he made slow but steady progress until his pubis mashed against hers. He put her legs over his shoulders to fully seat himself and paused to let her accommodate his size.

She looked up at him adoringly, “Nothing has ever made me feel this good, ever.”

Still staring into her eyes he pulled back a couple of inches and pushed into her strongly. She moaned softly, closed her eyes, and lifted her hips. He pulled back again until half his dick was in her. She caught the idea and bucked up as he pushed down. Another small sound and soon he was pulling almost all the way out, then slamming into her. She was arching up strongly, meeting his thrusts with her own. She was quiet compared to Sara. She writhed, gasped, and clutched the bedspread as her hips moved constantly. Then a powerful orgasm was upon her.

Her muscles clenched and she hissed, “Harder, Jake, it feels so gooooood!”

Jake slammed into her and ground his crotch against her clit. Her eyes flew open and she stopped breathing. She shuddered once and then all hell broke loose. With a high-pitched keening noise, she started thrashing all over the bed. Jake had to lean back on his knees to keep from being thrown off the bed. He palmed her tit’s and pinched her nipples and she flung herself against his groin violently. Her pussy was clenching rhythmically and strongly, clamping his dick in a velvet vise. After about thirty seconds, she inhaled deeply and fell back on the bed, letting her legs slip from his shoulders.

“That was incredible,” she said. “And you are incredible, I didn’t know I could come that hard. I almost passed out.”

Jake flexed his iron hard shaft still buried deeply in her slit. “We are just getting started.”

Debbie was the most athletic fuck of Jake’s two lifetimes. She threw her tight body around with abandon and matched Jake stroke for stroke. She assumed every position Jake wanted her in and orgasmed five or six times before he put her on top. This was the position made for her and she went wild. Her hair was whipping across Jake’s face and chest as her hips oscillated up, down, and back and forth. She came once that way and then headed for the big one. Jake had been desperately holding off his own climax and decided to let her get them both off. He snaked his hand around her smooth muscular ass cheeks and, when she leaned forward to grind her clit against his pubic bone, pushed his finger into her anus. That did it. She froze above him and her pussy started to spasm mightily, milking the cum from his balls. When his seed splashed against her womb, she looked at him and her cum intensified. Debbie gave a grunt, her eyes rolled up in her head, and she fainted.

Jake caught her as she slumped sideways and put her on her back in the middle of the bed. He hurried to the bathroom and wet a washcloth. He was gently wiping her face and chest when she came to. He lay beside her and took her in his arms. Finally she recovered enough to speak.

“Wow, will it be like that every time?” she asked.

“Probably not,” Jake said, “Today you were discovering your sexuality, and it was all new. But I promise that I’ll always try to make it this good for you.”

“I know you will,” she said lovingly.

Then with her wicked smile, she changed the subject.

“Sara said I should ask you to take me around the world.”

Jake gave her a leering grin of his own.

“Let’s take a shower and we’ll start the trip,” he said.

The shower was lots of soapy, slippery fun. Jake still marveled at her body. It was so firm, fit, and curvy. They toweled each other dry and tumbled back into the bed. Jake wasted no time before he attacked her pussy with his lips and tongue He licked, sucked, and wormed his tongue into her sopping slit. Debbie started her now familiar hip movements against his face. She cooed and gasped through a couple of orgasms. Then Jake flipped her onto her stomach and slid his throbbing cock into her still tight cunt in one long slow stroke. She was coming even before he hit bottom. He reached across her, grabbed the big plastic bottle of baby oil, and squirted some on her ass and his hand.

He flipped shut the cap, put the container next to him, and then started slowly pushing his slick fingers into her ass. Debbie waggled her ass in a mixture of apprehension and appreciation then laid her head on the pillow, pushing her ass up even higher. First one finger, then two, opened her up. Jake got more oil and squirted a stream into her crack. He grabbed her hand and pulled it to her clit. Debbie was in the middle of a hard climax when he pulled out of her cunt and positioned his prick at her sphincter. She only grunted when the head of his staff popped through her rubbery ring. Jake stopped to let her adjust to his intrusion and, when she started pushing back on him, he slowly stroked in and out, getting deeper with each lunge. Debbie started coming again.

“Oh! Shit! Oh shit, oh, Jake it’s soooooo big in me, I can’t stop cumming...” she chanted. “Harder, baby, fuck me harder, push it in deeper.”

Debbie began babbling.

It excited Jake to hear her talk so nasty.

“Whose ass is this?” he asked.

“It’s yours, Jake, all my holes belong to you.”

“What if I want to do you like this while you sixty-nine Melissa Thornton?”

That put her over the edge. Her butt cheeks clenched so hard he thought she would break off his dick. She bit down on the pillow and quivered. Jake pinched her clit between his fingers and her head snapped up. She gave an unearthly moan and a stream of liquid shot out of her pussy and soaked both their thighs and the bed. The pent-up semen spurted from his balls and his dick pulsated in her ass causing her to gush even more nectar. Sated, she fell forward. Jake followed, draped across her back. Jake started to get up but Debbie wouldn’t allow it. They rested like that for about ten minutes. Debbie said she like being held down by him. He filed that nugget away for another time, then stood up and slapped her taunt ass cheek sharply.

“Up, woman and bathe me,” he mock-ordered.

She giggled, “Yes, my lord.”

And she did an excellent job. He was squeaky clean, especially his dick from which she nursed another small load of cum without losing a drop.

When Sara arrived at two in the afternoon, the linen was changed and the bedroom was aired out. The sheets and spread that Debbie soaked were in the dryer. The siblings were sitting at the kitchen table looking innocent, fresh, and wholesome. Sara took in the scene and burst out laughing. Debbie actually blushed when Sara asked her how her trip went.

They all burst out laughing when Debbie quipped, “It was great but I got a little sore in Australia ... you know, Down Under.”


That night Jake and Cindy went on their first date. They went to a movie then Cindy drove down and parked on the beach. She faced her little Fiat towards the open ocean and they watched a fat full moon shimmer just above the wave tops. They reclined the convertible’s bucket seats and quietly enjoyed each other’s nearness. Cindy turned to face him with a serious look on her face.

She said, “Jake, I love you, and one day you are going to marry me and I’m going to be all the woman you’ll ever need. Until then I am going to save myself for you. You can see other women and do whatever you want as long as I am number one in your heart. I might date and even experiment but you are going to get my cherry on our wedding night, understand?”

He gulped and nodded.

“Besides,” she said teasingly, “you know I like girls, too. If you share, I know lots of nasty Catholic school girls.”

Jake was floored. He drew her to him and kissed her lovingly. The shifter got in the way but Jake didn’t mind. He was happy just being with her.


Monday found Jake well rested and ready to begin another week in paradise. As he walked into school he was repeatedly congratulated on his playing Friday night. Debbie’s cheerleading teammates were all over him. Melissa Thornton dragged them off and blew him a kiss. He made his way to homeroom and Mrs. Greer gave him a sweet smile and congratulated him also. She asked if he could drop by after school for a minute, just before practice.

It was good to be him that day. While he and his lab partner, Scott, tried to eat lunch, a steady stream of well-wishers stopped to talk to him and Ray Robinson. At Jake’s instigation, Debbie had assigned a sophomore JV cheerleader to keep Scott amused. Scott was tall and lanky but cleaned up well. He was personable and witty. Jake liked him and so, it appeared, did the cheerleader. Scott, however, really had eyes for Angie, Jake noted. Hmmm, they’d make a nice couple if you didn’t mind their children being ten feet tall and weighing fifty pounds.

At his last period study-hall, Jake was leafing through a book on abnormal brain function when the bell rang. He took the book up to Miss Doane and asked her if it was too late to check it out. She told him it was a reference book and that it couldn’t leave the library. She walked back with him to the stacks and found a general work on the same subject. He said thanks and impulsively picked her up and twirled her around. She giggled gaily as he sat her down but did not release her. She looked up at him, rose up on her tiptoes, and kissed his lips. Then, still giggling, she ran out of the stacks. When he got to her desk, she blushed and handed him the book, already checked out.

Jake walked to Mrs. Greer’s classroom and knocked on the closed door. She opened it and, he noticed, locked it behind him.

“Jacob, I owe you a big debt of thanks. What you told me hit home and your advice has brought back the joy I felt when I first started teaching. Now I look forward to coming here and hate to leave when school is dismissed. I wish you had some advice for the other parts of my life,” she said.

“Well, Vicki,” Jake ventured, “I just might have some.”

“I’ve never let anyone call me that, Jacob.”

“Exactly,” he said, “but wouldn’t you agree that I’m not just anyone?”

She laughed and said, “That’s for sure. Okay, it’s ‘Vicki’ when we are alone.”

“It’s ‘Vicki’ when we are alone or with people who don’t know us,” he countered.

She was intrigued, “It’s a deal.”

He changed the subject. “Stand up, Vicki. Let me look at you.”

She hesitated for a second then stood up and pulled her shoulders back. She had been to a superior finishing school and knew how to carry herself. Jake twirled his fingers around and she slowly turned in a circle. This was embarrassing, but exciting. Jake seemed to think for a minute.

He finally said, “You need a tight calf-length black skirt, black hold-up stockings, three inch black heels, a white blouse with ruffles and a bow at the throat, and sexy underwear. Try to have them for Friday and the pep rally. Meet me at the Seven - Eleven on Ridgewood tomorrow evening at 6:30, Wear jeans, walking shoes, sun glasses, and your hair in a pony tail.”

“Yes, Jacob,” she said.

Jake stood and held out his arms and for the second time in fifteen minutes he had an excited teacher in them. She was disappointed when he just hugged her and brushed his lips across her cheek.


Coach Nelson gathered the team in the athletic department’s classroom. With no fanfare, he showed them film of their next opponent, Central High, a Division 6A powerhouse from Orlando. Jesus, they were so big and sharp, they looked like a college team. Their defensive line was a big as the Dolphins’ front five and their wishbone ground game was as dominant as Oklahoma’s. Everyone sat in stunned amazement. Then Jake stood up.

He said, “Coach, I think I know how we can beat these guys.”

Jake went to the front of the room and started drawing x’s and o’s. Coach Nelson grasped what Jake’s plan was and excitedly said it might work. He sent the team out to the practice field and told them to limber up and set up in defense and offense. Fifteen minutes later he and his assistants came out with a sheaf of plays and formations and they got busy.

A new cheerleader picked him up after practice. His teammates were almost blasé about it even though she stuck her tongue so far down his throat she almost gagged him. Cindy’s show must have set the bar too high.


On Tuesday, time crept by. School was good, practice was intense, and Debbie picked him up afterwards. He was in a hurry to be dropped off. He didn’t want to be late for tonight.

At 6:30 sharp, Jake roared up to the Seven - Eleven on Rafe Robinson’s Kawasaki 450 motorcycle. Vicki Greer was standing around the side wearing surprisingly tight jeans and a white shirt. Her long brown hair hung straight down her back in a single long braid that almost reached her butt. She looked exotic and nothing like her schoolteacher persona. Jake was impressed. He pulled up next to her, handed her a helmet, and told her to climb on. She eyed the bike suspiciously but climbed on and wrapped her arms around his waist. He gunned the engine and sped out onto the highway.

Jake pulled onto a little used country road and wound the bike up. Although he was only doing 55 the feeling of speed was exhilarating.

Vicki put her mouth to his ear and yelled, “Jacob, I love it!”

Jake nodded and found the turn-off Scott had told him about. He followed the dirt road to a Boy Scout camp only used on weekends, and during the summer. Jake turned off the bike and took off his helmet. Vicki did the same. Without speaking, Jake took her hand and led her to a picnic table. He sat on the tabletop and pulled her to him until she was standing between his knees.

“This is what else you need,” he said and kissed her.

She kissed him back fiercely, her tongue dueling with his.

A thoroughly enlightened Victoria Greer went home that night. Her pussy still tingled from being licked for the first time, and the first load of cum she had ever swallowed rested warmly in her stomach. She hummed to herself, as she got ready for bed. Tomorrow she would buy some new outfit’s and shave her pussy. She would also make the Saturday reservations at a Daytona motel, right on the beach like Jacob wanted. They had not had straight intercourse but Jacob said to be ready for Saturday. She couldn’t remember when she had looked forward to something so much.

When Bill Greer arrived home from the school board meeting, he was pleasantly surprised to find his wife asleep. No argument about his long hours tonight he thought, as he slipped into bed. As a matter of fact, from that day forward he seldom received criticism for all the hours he worked.


Wednesday morning was a treat for Jake. Mrs. Greer was classily dressed and her lecture was scintillating. You could see her enthusiasm for her subject and her students responded positively. Everyone was attentive and discussions were lively and focused.

Geometry went well, but the high point of the day was chemistry. Scott and Jake were running some tests to try to analyze a liquid they had been given. They found one element right away but had run fifteen of the workbook’s tests and still had not found the second.

Mr. McClelland cleared his throat a second time before Jake looked up. When he did he almost fell out of his chair.

“Students,” McClelland said, “this is Erika Johansson. She is transferring here from Minnesota. Since everyone has a lab partner, Miss Johansson will work with Mr. Turner and Mr. Hughes. I am sure they will work diligently to help her catch up.”

Mr. McClelland walked Erika over to their table. She was a Nordic Goddess, six feet, two inches and one hundred and sixty pounds of Scandinavian perfection. Her corn silk hair was done up in two braids, her peaches and cream complexion was flawless, and her body was perfect. She was the most intimidatingly beautiful woman he’d ever seen. She made direct eye contact with Jake and arched her eyebrows when he did not look down from her challenge.

Still looking into his soul with those sky blue eyes, she stuck out her hand and said, “Hi, I’m Erika.”

Jake enfolded her hand and held it, “My name is Jake Turner, your date for the Homecoming Dance.”

She looked at him solemnly, “Yes, you are.”

Scott’s eyes were bouncing between the two like hyperactive pinballs. Jake released her hand reluctantly.

“This is Scott, our only hope for passing chemistry, so be nice to him,” said Jake.

She turned and held out her hand to Scott, “I will be. Nice to meet you, Scott.”

Scott put out his hand but avoided her frank stare and could only mumble something incoherent. This was the normal reaction she got from men.

After chemistry, Jake included Erika at his and Scott’s table. The usual crowd came and went. Jake noticed that Erika seemed to intimidate both men and women. The only other person who didn’t seem bothered was Angie. After they had been seated for about five minutes, Jake felt a presence behind him. He turned his head and looked up and then up further.

“Is this seat taken?” said a very large, very blonde guy.

“Nope, have a seat, it’s yours” said Jake.

The big guy sat between Jake and Erika.

Erika laughed and said, “This is my younger brother Erik. He is always trying to scare boys away from me, like I needed the help.”

Erik joined in her laughter. “Younger by two minutes,” he explained.

Jake made introductions, “I’m Jake Turner, this is my really older sister Angie, and these are my buddies Scott Hughes and Ray Robinson. I sure hope you play football.”

“I do, I was hoping to try out for the team today,” Erik said.

“What position do you play?” asked Ray.

“At my last school I played tackle on both sides of the ball,” Erik said.

Jake threw his arm around Erik’s massive shoulder and said, “If I wasn’t already in love with your sister, I’d kiss you.”

Every one at the table cracked up except Erik who looked at his sister in confusion.

“I’ll tell you later,” Erika told him.

Erik fit right in with the Kennedy football system. He was as strong as an ox and surprisingly quick. He was intrigued as the team prepared for Central High. He had never heard of half the things they were going to try.

Erik was in front of the gym with the usual suspects when the little Fiat swerved into the lot. Both doors opened and out stepped Cindy and a girl who looked like her twin. Both had their blonde hair in pigtails. They wore the identical stripper version of their school uniform: saddle shoes, knee socks, short skirts, and white shirts with the top buttons undone. The pair ran up to Jake and started kissing him. They each took a hand and drug him toward the car.

Cindy turned to the stunned team and said, “I hope you didn’t tire him out because we want to play with him now.”

The girl Jake did not know pushed him into the passenger seat and climbed into his lap. Her tight little ass was perched atop his growing erection and her perky boobs were brushing his face as they roared onto the highway, leaving some very open mouths behind.


Jake arrived at school Thursday feeling like a million dollars. With a wry grin he thought why shouldn’t he. Things just seemed to go his way, a far cry from his first try at high school. At times he worried about how long his good fortune was going to last, but today was not one of those times.

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